Musical World Tour: The Best Songs About Chicago

Last week we started a semi-regular feature wherein we look at how different cities have been immortalized in song over the years, from celebratory anthems to warts-and-all depictions of seedy urban underbellies and the dark corners where good folks just don’t venture. We got some excellent suggestions and feedback from our readers when we started the idea right here in New York City, and this week we head to the Midwest to choose our five favorite songs about Chicago. Let us know your suggestions after the jump!

Sufjan Stevens — “Chicago”

The centerpiece of Stevens’ rambling masterpiece Illinoise is a simple travelogue of a voyage to the Windy City and back… and yet, it’s also so much more than that. For all the at the lyric’s ostensibly pretty simple — it apparently catalogues a journey the singer and a couple of friends to the city for a weekend when he was 19, when they were broke and ended up staying with a couple of homeless men in an old school, and contrasts that trip with a later visit to New York — it also embodies many of the central themes of Illinoise, including self-discovery, change, renewal, the desire to run away and start again, and the discovery that ultimately it’s not where your body is that matters… it’s where your heart is that counts.

Nick Cave & the Bad Seeds — “In the Ghetto”

Yes we KNOW this is a cover version (although, it has to be said, Elvis didn’t write “In the Ghetto” either — it was in fact penned by Texan songwriter Mac Davis). We just happen to have a soft spot for Cave’s version, which was his very first single with the Bad Seeds and features a video that looks like it was shot in his parents’ garage (in fact, it was shot in the garage of a house in LA, where Cave was living at the time). Anyway, whichever version you choose, this is a fantastic song about the atavistic social ills of poverty, set against the backdrop of a “cold and grey Chicago morn.”

Marshall Jefferson — “Move Your Body”

Wait, can a track whose lyrics have pretty much nothing to do with Chicago still be about Chicago? We say: yes. This is perhaps the quintessential Chicago house track, and the spirit of the city in the mid-1980s permeates every aspect of its sound — it’s a record that makes you feel like you actually really are at some sweaty mid-Western warehouse party in 1987, even if (like Flavorpill) you were all of nine years old at that point.

Dr West’s Medicine Show & Junk Band — “The Eggplant that Ate Chicago”

So… maybe the acid really was better back in the ’60s, eh? (Sorry for the bodgy video, by the way — there’s a better version here, but it has embedding disabled.)

Robert Johnson — “Sweet Home Chicago”

The Great Migration that brought some six million African-American workers into the North increased Chicago’s population by some one million people between 1900 and 1920. The immigrants brought their music with them out of the south, and by the mid-20th century, Chicago was the home of the blues north of the Mason-Dixon line. There have been many fantastic Chicago-based blues musicians since — Buddy Guy, Muddy Waters and Bo Diddley spring to mind immediately — but if there’s one blues song that’s become a de facto anthem for blues and the Windy City, it’s Robert Johnson’s 1936 depiction of the city as some sort of distant promised land (indeed, he equates Chicago with California, a lyric that’s inspired much debate over the years). In the 75 years since Johnson’s version was released, “Sweet Home Chicago” has been covered by everyone from Fleetwood Mac to The Replacements — but we still like the original best.